My children are 3 and 5. They have both outgrown naps at home, but Disney is super stimulating as we all know and sometimes they nap there. I have always let them sleep in the stroller. My kids were never the type to take naps in beds (usually they napped in the car), so it never made sense for us. Furthermore, if they were tired, the long stroller ride to the bus stop followed by the ride on the bus would have them asleep before we got back to the resort. Do consider bringing or renting a stroller large enough for even "big" kid preschoolers to sleep in. Also, we now really enjoy staying in a 1 BR villa to have the extra space, even if that means we take a shorter trip.